Disulfides and boryl sulfides serve as both initiators and precatalysts in radical reductions of halides by an N-heterocyclic carbene×Borane

Article abstract of DOI:10.1002/adsc.201300752

Diphenyl disulfide (PhSSPh), a typical boryl monosulfide (diiPr-Imd-BH ₂SPh) and a typical boryl bis-sulfide [diMe-Imd-BH(SPh)₂] all serve as both initiators and precatalysts in the reduction of alkyl and aryl halides by readily available 1,3-dimethylimidazol-2-ylidene×borane (diMe-Imd-BH₃). The reactions are suggested to occur by a polarity reverse catalysis mechanism where in situ generated thiophenol is the active catalyst. Copyright